posted this in Investor Alley also just getting a diff perspective:
just making sure I have the simple tax rules understood for my 2019 situation, company got bought out last year so took a nice package and good amount of time off, just went back to work a couple months ago and will end up with about $40K income for 2019.
Have a decent amount of company stock (both through ESPP and granted options) that I could sell/exercise at anytime (MDT - currently at all time high), just checking it would be advantageous tax wise for me to sell/exercise enough stock to amount to ~$13k of net gains (a bit complicated to calc since ESPP was at 15% discount-and value has grown 30-50%, and options granted ~60% of current value)
since I can add about $13K LTCG to my 2019 income and with the standard deduction pay 0% CG?
I don't actually need the funds for anything and don't mind holding the stock, just wanting do what makes most sense tax wise here, would send any cashout straight to VTSAX
or alternatively should I roll my old 401K into a traditional IRA and covert $13K to Roth at 12% fed tax rate? would this be more tax advantageous long term since future gains on the converted amount will be untaxed?
